Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.

Serreta Boson

I remember sitting in church and listening to a sermon about being a WATER WALKER. It’s the story about in the midst of a storm Peter walked to Jesus… he was walking on water. BUT THEN HE LOST FOCUS…. I said on that day I wanted to be a water walker. Life goes on and I get hit with a hard blow. I had to have brain surgery. The surgery was scary but I had to walk on water. I was told I would no longer be able to work. I had to walk in water. I took my father’s recipe for making pickles and started a company. Read more>>

Angela Mabe

It was a risky decision, but my husband Mark and I were determined to make our furniture company, March Legend, a success. We left our city life behind and headed for the wilderness, where we built a small cottage while pursuing our dream. Our home was a tent, but we didn’t mind the discomfort. We were committed to making our business work. After the cottage was built, we began building furniture downstairs while we lived upstairs. It was challenging, but our passion for our craft drove us. We knew we could build something extraordinary if we were patient and persistent. Read more>>

Tabby Biddle

I was 26 years old and working at my dream job at the National Geographic Magazine in Washington, D.C. I’d been with the company for four years building my career as a young, rising journalist. I had my own office with a big window that looked out to “M” street and the daily movements just a few blocks from the White House. I had great, supportive, friendly colleagues at the company. I was getting paid well. And I was the captain of the National Geographic Ultimate Frisbee team, which was a ton of fun. All to say, life was good. Read more>>

Robert Hill

When I started Stoned Panda Beatz I had very little money, I was trying to raise my profile across social media platforms by any means possible. One day I decided to risk it all and put all my time into my craft. I started making flyers on my own. I put them up in various towns and venues before moving onto making stickers. It made me nervous to put myself out there as a businessman but the risk of failure didn’t stop me. I started going to events, passing out flyers and stickers, and people really took notice. Now Stoned Panda is a a recognizable name, and more people want to hear my new music. If I had not taken these risks I would not be where I am today with Stoned Panda Beatz. Read more>>

Mindy Kittay

Embarking on the journey creating The Kama Connection was a risk that reshaped my entire trajectory. After a fulfilling career as a library director, I craved the opportunity to use my creativity but I wasn’t sure what that would look like so I decided to fulfill a life long dream of travelling the world with no agenda for a year or more. I made it to Costa Rica and Bali and then Covid happened and I had to return home with no plan. Soon after friends began to encourage me to open a store in Joshua Tree (near where I was living), in order to sell the jewelry and meditation tools I was creating. This was not something I had thought about and certainly not during a shut down but rents were low and Joshua Tree was incredibly busy as city dwellers wanted to be out in nature and not locked up in their homes and apartments. The risk came when I decided to take the leap and transition to entrepreneurship, opening an ecommerce and brick and mortar store. Read more>>

Torii Rurup

Like many others, I lost my television production job when the pandemic hit in March 2020. After months of lockdown, tons of free time on my hands and reflecting on my life and career, I decided I never wanted to go back to the toxic work environment that is the entertainment industry. After-all, I had tons of other experience in different industries, and I am the type of person who wants to always learn and try new things. Read more>>

Desiree Ve’an

The biggest risk I took was starting Casually Threads. Everyone who has known me for years has known that I’ve wanted to start a clothing line for years now. I was too afraid to take the risk and do it. I was afraid that I was going to fail and that my ideas weren’t going to be good enough. Then one day I woke up and decided to just take the risk. I didn’t want to be old and grey sitting on my front porch thinking about what I could’ve done. If it fails in the end at least I can say I tried instead of saying I never tried. Read more>>

MaQuade’ “Angel” Allen

2018 11th grade education! No money; just got released from jail to probation; my last mistake was my wake up call! I knew I had to make a change or the streets would take my life! I went back to my mom’s house in Oak Cliff Texas thinking I could start over there, but she wasn’t having that so I had to make it on my own. Took me a few days, giving plasma, labor ready, doing anything I could to make some money. I finally got enough to get my own apartment, but I knew that wasn’t enough. I wanted to go back to school but didn’t know how. I looked up a school that would help me get my ged and enrolled into NorthLake College GED program. Read more>>

Sintia Magana

A Leap of Faith into the World of Cosmetic Tattooing Life often presents opportunities disguised as challenges. During the peak of the pandemic, I found myself at a crossroads, battling feelings of helplessness and despair. The revelation of 3D areola tattooing became my beacon of hope, inspiring me to embark on a journey into uncharted territory. I took the plunge, enrolled in my first course, and the rest, as they say, is history. The decision to step into the realm of cosmetic tattooing was a risk worth taking. Little did I know that this leap of faith would not only lead to personal fulfillment but also allow me to make a significant impact on the lives of others. Read more>>

Jordan McCray

Graduating from Full Sail University for me was a big risk. I say that because around the time of enrolling my first child had just recently been born, and I knew school was going to be equally time consuming. Not only that, but I was still working a Full-Time job on top of joining the Parent Club. Read more>>

Tausha Nunez

In January 2023 I was informed the company that I was a founder in was going to be closing its doors. I was offered to hop into another opportunity as a founder again. This company had no name, what I knew about it was that my CEO was going to be coming over and so was my companies Chief Scientific Advisor/Formulator. The investment was something my family didn’t have at the time. But knowing this was a ground floor opportunity with products that had already changed my life and many others, I took the leap and found a way.  Read more>>

Lindsey Macdonald

I feel like moving to Colorado was a huge risk I had to take to better my life. I was very apprehensive initially coming out here. I had lived in the panhandle of Florida for 21 years and knew that area like the back of my hand. I wanted to be with my family which was propelling me of course but I was very scared of going to a new place where I didn’t know anyone. Read more>>

Alicia Long

When you take the time to reflect on life’s choices and identity the defining moments, it makes you realize the risks you had to take to in order for the outcomes to turn out the way it did. I believe my first major leap of faith I took was in myself. My aesthetic career started before this major moment but the decision to take a job where my lively hood was completely based on performance. IT was an EAT WHAT YOU KILL type of situation. The platform was set up for success, but it was on me to make sure I was successful. My husband and I had made things work for our family durning nursing school on a tight budget and faith, so we knew could do it if things were rough. His support and our strength made it possible to jump headfirst into somethings that would launch my entire future. Read more>>

Anna Scott

Locksley Shoemaker

Everyone talks about going out there and “getting after it’, but to actually do it and open a business takes a lot of courage, work and dedication. After high school I had bounced between different jobs, but none of them really felt right for me. I’d always been interested in martial arts from a young age and had at this point been trying out Jiu-Jitsu and Mauy Thai, but still hadn’t really found my niche yet. Read more>>

Macie Melton

My biggest risk was turning my small dream into an LLC. I started The Downtown Dirty in the summer of 2019 and once it started gaining a following and attention it took me by surprise how much it meant to people. It pushed me to take the business to the next level and expand. When doing this I invited others in to possibly partner as I was doing it all solo. I learned very quickly how important it is to make sure you have all your business needs together before taking such a move forward. It took a rough turn that made me take the leap of faith and register my dream and hobby as an official LLC. I am now the Owner and Founder of The Downtown Dirty and continuing to work it in the best interest of the Small Businesses I represent. Read more>>

Michael Chester

First of all, I would like to say how grateful I am that I get to share this story. Interesting enough, answering this question transparently, even today, presents itself as a risk in my brain. Fortunately for me, the same value that helped me make room for the risk in the story I’m about to share is the very same value that is helping me get this out–despite the perceived risk in doing so. Read more>>

Maddison Hill

In 2020 I made the decision to leave my full time hosting and producing job at a digital entertainment news network in order to pursue creating content on my own and for myself. Unfortunately, due to new ownership the work environment had grown incredibly toxic and as opposed to continuing to work in an environment that was not conducive, I made the choice to leave and start something on my own. Read more>>

Phillip Banks

Taking a risk is scary. Big or small, it’s a courageous action. No matter what we do on this earth, we are going to pay a price. You can’t escape making a choice and there will always be risky opportunities. You’re either going to pursue the dreams placed in your heart or help someone else pursue theirs. Life isn’t like the movies though, sometimes you take the biggest risk of your life and don’t walk away with what you expected. The only thing you can expect is to walk away with is an experience and a lesson. You can’t think too much about taking risk, you must decide to make a plan and stick to it. NO MATTER WHAT. There’s something for everyone over that wall of fear. Comfort is where dreams go to die. You either take the risk or get finessed by life. Read more>>

Kelsie Johnson

When I was pregnant with my youngest child in 2021, I was faced with the tough decision of either going back to my full time job, or taking the plunge in going full time in my business. This is something I’ve always dreamed of doing, but was fearful of. Scared I wouldn’t be able to provide for my family, scared of failure if it didn’t work out. After he was born I knew I didn’t want to leave him to go back to work so I took the risk! With the support of my husband, I quit my job and decided to go full time with my photography business! The first few months were a little scary. Read more>>

Stephanie James

The biggest risk I ever took was quitting my 8-year job at a Fortune 50 company—the first job I got after college. No safety net, no backup job. I got accepted into a program that let me live in a different country each month for a year. It was a now-or-never kind of opportunity. I loved my job, but the allure of exploring the world won me over. I always advise taking a leap of faith, but it’s crucial to ensure it’s a calculated leap, make sure the waters are deep enough and you can swim to shore afterward. My desire to see more of the world started after interning at the 2008 Summer Olympics in Beijing. That experience opened my eyes to a whole new world, and I knew I had to explore it. That’s when the travel bug bit me. Read more>> 

Dianne Shelton

Roughly 11 years ago, I took the biggest and most transformational risk in my entire life: I co-founded, co-owned, and co-created an amazing Spiritual and Personal Development center in the heart of Austin, Texas called The One Center Austin. We started from scratch looking for a commercial property; sought out funding from the SBA and local financial institutions; wrote a solid business plan; oversaw a complex remodel of the property; and opened our doors in 2014. We provided trainings for groups; weekly events; and worked one-on-one with individual clients. Read more>>

Nona Djavid

When I first launched my private practice, I used the universal chiro checklist. The one that tells you how to brand your practice, price your services, and increase revenue slowly over years of repetitive action. I was building a practice based on someone else’s goals. It wasn’t until I interrupted my pattern of engrained (mis)behavior, that I quantum leaped right into a thriving, successful practice. Read more>>

Olivia Leitstein-Yong

One of the biggest risks I recently took was quitting my graphic design job with a stable pay to be more selective about the design projects I work on and create Mystic Path, my design business. I knew it was time to double down on my own personal style and trust that aligned opportunities will come. Mystic Path has become a platform for a lot of my own art projects, but it’s also available as a service for anyone who likes my work and wants to collaborate. I’d say it specializes in merch creation, and anything music related, such as event flyers, concert posters and festival branding. Read more>>

Dr Zee Celest

Over the course of my life, I’ve displayed a proclivity for embracing risk. As the fourth of five children, raised in a household guided by a religious mother, I consistently found myself testing the boundaries and challenging established rules. I was unafraid to take risks, even if it meant the possibility of facing trouble for my covert participation in school activities such as sports and dance. Despite the lack of resources or guidance to support my dreams, I remained steadfast in my belief in my own talents, resolutely showcasing my creative abilities. In due time, my mother came to appreciate that I harbored my own aspirations. Read more>>

Jeffrey Mandelkorn

As a psychologist working in private practice, I get to learn about my clients’ childhoods and influential early life experiences. These conversations inspire and motivate my own introspections and reflections regarding my childhood. I have a tremendous gratitude and a lot of positive feelings surrounding my upbringing. One strong influence gleaned from my childhood was a sense of being risk-averse, specifically when it comes to financial issues. On its face, minimizing risk makes sense, no one wants to assume more risk than necessary. Read more>>

Nelia McNicol

I was born with a deep desire to work in the arts, fascinated by story telling through the medium of theatre, film and television. I was dancing and performing from as early as I can remember and dreamed of being on Broadway. When I was 17, I was accepted into Joffrey Ballet Schools Jazz and Contemporary 4 year trainee program. I knew that the opportunities and people I was meant to meet and work with were on the other side of the world so I left the small coastal town where I grew up in north eastern Australia and set off to NYC. Read more>>

Nancy Metayer Bowen

The decision to enter local politics was a significant risk. In the City of Coral Springs, I ran for Mayor and later Commissioner, competing against multiple established candidates with significant name recognition. As the first Black woman and Haitian-American, the challenges were evident. Despite the odds, I remained true to my core values and community-centric vision. Read more>>

Nicole Ponce

A recent risk I took was taking a leap of faith in opening a Holistic Wellness space in Sugar Land. I have owned my private therapy practice for almost seven years and always felt like I wanted to bring more to the local community than what I was offering. When I met my current business partner and friend, Meaghan, she shared a similar passion. Quickly, we realized that we had a calling to create more healing in our local community. Read more>>

Gino Bambino

Putting my name in the band name. I figured getting and keeping a band of the same people would be difficult, plus I was moving around quite a bit at the time so I knew, I guess. I knew I’d have to do everything, not that I didn’t have some help along the way, but primarily it’s on me. And good or bad, i’m to blame. ha. So far it’s worked out ok. Still a long way to go so we’ll see. Read more>>

J’Atelier9 ™️

All life is risk.. So taking a risk to leap into an ambitious endeavor as a sustainable artisan visionary became a natural risk for me.. where fate and intuition would allow my imagination to flourish.. In fostering a sustainable discipline and movement, there is the inherent risk in transforming my ideas and concepts into unconventional mixed mediums and pushing boundaries outside the confounds of traditional fine art. Read more>>